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Ep 48: How a Pilot turned into a CEO: Ben Klein, CEO at Aero
68 Plays3 months ago
How do you build a legal and business career from a passion for aviation? What is the transition like from the GC role to that of CEO? And what is it like to run an airline?
Ben Klein, CEO and First Officer at Aero, was able to combine his dedication to legal work with his lifelong love of flying. Starting off at big law firms like Davis Polk & Wardwell, he successfully transitioned into aviation law after founding his own firm, then took on GC roles at autonomous helicopter start-up Skyryse and Aero, an airline offering a private-jet-like experience.
Listen as Ben discusses instilling confidence in investors during a CEO transition, counseling his airline through the coronavirus pandemic, and leveraging his experience in the cockpit to make his company the best it can be.
Read detailed summary: https://www.spotdraft.com/podcast/episode-48
Topics:
Introduction: 0:00
Transitioning from corporate law to aviation law: 6:01
Founding an aviation-focused law firm: 9:38
Learning to manage an executive team as a first-time GC at Skyryse: 11:47
Counseling an airline through the coronavirus pandemic: 14:57
Taking on a GC and First Officer role at Aero: 16:09
Leveraging your experience in the cockpit to lead as CEO: 23:59
Instilling confidence in investors as you transition from GC to CEO: 25:47
Inspiring teamwork in c-suite reports and hiring for your replacement GC: 30:58
Book Recommendations: 35:30
What you wish you’d known as a young lawyer: 38:49
Connect with us:
Ben Klein - https://www.linkedin.com/in/ben-klein-01b8736/
Tyler Finn - https://www.linkedin.com/in/tylerhfinn
SpotDraft - https://www.linkedin.com/company/spotdraft
SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.
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Transcript
CEO's Innovative Ideas and Team Dynamics
00:00:00
Speaker
there's There's not ah ah a day I fly and probably to the chagrin of many people on the team or I don't come up with some new idea of how to refine or or change what we're doing in the operation based on.
00:00:18
Speaker
How do you build a career around a passion for aviation when that was never even part of the plan? What's the transition like from the GC role to that of CEO? And what's it like to run an airline?
Introduction to Ben Klein and Arrow
00:00:31
Speaker
Today, we are joined on the abstract by Ben Klein, the CEO of Arrow. Arrow offers a private jet-like experience by the seat on flights to destinations like Aspen, Sun Valley, Los Angeles, and Los Cabos. all nice places in either the summer or the winter, pretty much any time of year. Before taking on the CEO role, Ben was the first officer in and the general counsel, and before Arrow, Ben was the GC of Skyrise, an autonomous helicopter company. Ben also previously had his own law firm focused on aviation law, and he started his career at Davis Polk and Paul Weiss. Ben,
Favorite Destinations and Pilot Experiences
00:01:09
Speaker
thanks so much for joining me today for this episode of The Abstract. Absolutely. Happy to be here, Tyler.
00:01:14
Speaker
Uh, this is going to be a fun conversation before we get started on your career though. I'm curious, I listed out some pretty great places. What's your favorite destination that arrow flies to? And since you are a pilot also flies arrow planes. I'm curious if the destination that you yourself like to fly to is, is any different. Is there like a particularly cool airport that you like to land at? and Oh, well, I hate to good question. I hate to play favorites. But I think that it depends on the time of year to be frank also, right? But but sure, one place that I'd never been to actually until I started working at Arrow was Cabo. And I've been lucky enough to spend some time there in the past few years and I do love Cabo. I'm surprised by the amazing restaurants. I've had some of the best meals in Cabo, including a place we partner with called Flora Farms, which is a Cabo sustainable farm restaurant hotel located near San Jose del Cabo. so well I'll go with Cabo today, but you know if you ask me tomorrow, my answer might change.
00:02:21
Speaker
I was going to answer the second part. so in In terms of flying, Aspen is a unique airport to add into. Quite challenging given terrain and challenging even on on a nice day and many days in Aspen are not nice, which adds additional challenge. and We actually at Arrow, all pilots do recur training every year If you're a first officer, it's once. If you're a captain, you go twice a year. and As part of every training, we do a ah day devoted to Aspen, both starting process and in the simulator um because it's it's that and much of a unique ah sort of operation into the airport. For a pilot, you're on your toes and it's it's it's a lot of fun.
00:03:05
Speaker
I've been to Aspen a couple of times and I think both times we've been rerouted to Grand Junction instead of being able to land there. I actually don't know if I've ever landed in Aspen by plane before. yeah That's a common lament and you know what? it's it's ah
Passion for Aviation and Early Beginnings
00:03:18
Speaker
It happens a lot. Like you said, either if you fly the airlines, you're going to be rerouted to Cabo or excuse me, rerouted to Grand Junction or Denver. Sure. At Arrow, we're lucky enough to be able to divert into an airport called Rifle, which is only 45 minutes away. um and We've developed this whole seamless procedure where we send out cars to pick guests up in Rifle and drive them to Aspen. When we have to divert, which which happens just because of wind and and weather, it's if's not quite as inconvenient as ah is when you're going to Grand Junction or Denver.
00:03:53
Speaker
the one The one benefit of that, the one benefit of being diverted is maybe there's a snowstorm and maybe it means you're arriving for like a powder day the next morning. True. That's right, if you're lucky. If you're lucky. Ben, where did your passion for aviation come from? Was there ever a point in time where you thought that you were going to be a professional pilot? You know you always like to think that your passions and are somehow innate and and they're they're authentically yours. I can't remember a time not loving airplanes. But that being said, you know the sea must have been planted somehow in a way that my subconscious that i can't I can't really remember. But I, from an early age, begged my parents to give me flying lessons. And um believe it or not, they they relented when I was 12, and I took my my first flying lesson ever when I was 12 years old.
00:04:42
Speaker
Wow. so It's been something that like I cannot remember a time when when I didn't love airplanes. There was a time I'll say when um I went through a bout of air sicknesses, but when I was like six or seven, I remember routinely having to to use the ah the old bag and the seat box. um But yeah, other than that, to this day, i I spend an awful lot of time thinking about
Journey into Aviation Law
00:05:05
Speaker
airplanes. That's really cool. I mean, when other kids were picking up soccer or just sort of graduating to like baseball or were you reading operational manuals for aircraft in advance of of trying to get on one and fly one yourself?
00:05:19
Speaker
Well, you know I don't know if I got that technical, but but and i you know I was interested in all the other kids stuff also, but um but I did actually used to buy my father books about how to learn to fly for his birthday. It's sort of a suggestion because I thought if maybe I got him into it, it'd be easier. you know they And this is i but like nine or 10 years old. yeah So um I don't know about operational manuals, but i I was finding ways to learn as much as I could ah early on. That's cute. I mentioned, you know, you you worked for Paul Weiss and Davis Polk and and we're doing sort of corporate law. How did you make the transition to to aviation law? Because when we were prepping for this, it didn't sound like that was like what you knew you wanted to do for your career. It was something that came about a little bit by happenstance.
00:06:13
Speaker
Yeah, well, you know a lot of going to law school sort of came about by happenstance. I'm not going to pretend I'm not someone who put a lot of thought into the decision to go to law school in the first place. um i I don't think I ever considered going to law school in college, um really, not not once. And you know after college, I spent a couple of years doing things like you know waiting tables and bartending. and i yeah I felt some pressure to to get some some direction and and took the LSAT and and did well enough that I got into some some great schools. and sort of
00:06:52
Speaker
you know, that's as simple as the story of me attending law school, not not very inspiring. And I wouldn't encourage taking that approach, but that was mine. And then so, you know, because that, and let me say, I loved law school, was a, um you know, an intellectual awakening of sorts for me, I'd never been a great student. um And I just immediately found sort of what I was looking for in terms of an academic experience in law school, a way of thinking um that that work for me and i felt like i was a certain equally.
00:07:26
Speaker
well suited for, at least much more than math and science and everything else that I that i hadn't been so good at in the past. um and Then you know coming out of law school, um i justve I followed the well-worn ruts that are there and um and also you know the opportunity to make what seemed like a huge sum of money. It went down the the corporate sort of big firm route. I have to say, I had great experiences, met fantastic people, um learned a ton, um but it became pretty quickly you know apparent to me that it was not the right place for me, that I wasn't going to like
Building an Aviation Law Practice
00:08:07
Speaker
succeed in the way that I wanted to succeed um in that environment. and So you know I had to spend some time thinking, all right, here I am. right I've spent a lot of time and money ah getting a law degree. and what ah Where am I going to take this from here in a way that sort of makes sense and work?
00:08:23
Speaker
here I wish I could say that I had a Eureka moment law at a big firm. Well, it should be aviation law, but um yeah it was it was a much longer process than that. I left the big firms altogether. I went to work for a smaller firm. I was really getting my hands around running cases from start to finish myself, doing the kind of things you couldn't do at bigger firms, learning how to be a lawyer in a lot of different ways. And I'd learned that in a big firm environment. And after a year or so of that, I had my my first trial that i that I participated and involved in Airpoint.
00:08:58
Speaker
And that was just luck. And yeah all this time I'd been flying sort of on the side as a passion and a hobby, and it was still very much part of my life, but completely divorced from from what I was doing professionally. I think that was that was sort of the moment when I was like, okay, this is how i this is going to fit together here. And you know from then on, it was just a process of how do I make that work? Because this was just right, right? This wasn't I hadn't built out of practice. I wasn't aviation learn anyway. Yeah. And so there was there was the long process of figuring out how do I get from here to what I'm now envisioning where I might want to be.
General Counsel Role at Skyrise and Management Challenges
00:09:38
Speaker
How did you build that book of business then? I mean, and eventually when you start your own law for, you know, cause he wasn't like, you know, Oh, well I spent 10 years at the FAA and I have this regulatory background and I have been approving things for a variety of aviation clients already just on the government side. Like how did you actually go about and sort of build the book of business for yourself in the aviation space? Slowly. Uh, slowly. It was, it wasn't easy. You know, I, yeah. i found I was lucky early on I found one client um who had a fair amount of business where I was able to start. you know This was still litigation, so i was it was yeah breach of contract, breach of warranty kind of cases involving aviation.
00:10:24
Speaker
And then I started working with an organization that gives legal services to pilots at a discounted rate um in order to provide them representation before, you know, hearings before the FAA if they messed up somehow. or um And so learned a lot of the regulatory um side of things that way. And it was a multi-year process. I had to go out on my own, really pursue this just practice area, because no no firm, even a small one, was going to give me the time I needed to do these kinds of things, but you know to really develop. And it wasn't lucrative.
00:11:02
Speaker
you know, this, the yeah family work I mentioned is, you know, like I said, that was a legal services plan. It's, it's, it's not well pay work, but it's, it's a great education, you know? So yeah, I went out, I started my own practice and it was for a long time, still at least 50% plain vanilla commercial litigation. And then um slowly I built up the aviation piece of it over, over many years really. um But what helped of course was that, you know, I'm a pilot and I was a pilot of fan And so I'm always involved and I speak the language. And I think that was a big part of being able to gain the trust of a lot of clients, even if I didn't have necessarily the legal background, given that I spoke the language and I had that expertise, you know it went a long way.
00:11:45
Speaker
I'm sure. um When you made the the leap to become GC, first GC role at Skyrise, you actually worked with my first boss out of college, Bill Goodwin, who's a great guy. Was the learning curve being a GC for the first time steep, particularly on the on the management side? How do you work with these other folks? i mean I'll say for Bill, like someone who's very knowledgeable right about aviation policy and and now you're stepping in sort of from a small law firm that you've been running to a management role in i in a corporation with a legal team under you. What was that like? very Yeah, I was learning curbs steep, very steep. very yeah I came with you know as ah as a litigator who had been in private practice for 15 years at the time and I knew nothing about
00:12:35
Speaker
venture financing, IP, privacy, all these things that are sort of the key parts of of what ah a GC does, in a you know a venture-backed company, and and yeah or any company really, but a small company. and so there's There's an awful lot to learn. you know so you know I had to rely on one outside resources. right so Great organizations like the one you used to work for, and I'm still a member of TechGC. I guess rebranded as the L Suite. Yeah. Not sure how I would feel about that. But um but that that instrumental in in my in my making it as a GC early on, just the resources and the support. And you know, you have to sort of learn to trust yourself. And I think that my my background as as being a so you starting my own firm, sort of gave me that that confidence to be able to go into situations on my own, where I didn't maybe know as much as I should.
00:13:33
Speaker
and figure stuff out. Either figure out or or figure out who to ask. And so that was, I think, an important skill set that I did have that I that i could draw on. um And then, yeah, people like Bill, ah the legendary Bill Goodwin, right? Hilarious, gracious, ah hungry. and When I say hungry, I don't mean hungry in the ambitious sense. I mean, made a big big appetite. And brilliant, you know, in that order. i And yeah, I mean, so Bill was instrumental, you know, and and other just people that I met that I can rely on you've had that experience into work.
00:14:06
Speaker
as I said, just really gracious and giving me time and and ah and helping me learn.
Navigating COVID-19 at Arrow
00:14:11
Speaker
And you were actually tested relatively early on in that you were at Skyrise when when COVID hit um and you sort of had to help the business navigate all of the operational challenges and also sort of financial challenges that came along with that. How was how was Skyrise impacted and and how did you help the business weather that storm? you know I think in some ways, being in a pre-revenue venture back company that had money in the bank was a pretty good place to be in early COVID. yeah I mean, sure, the world was scary. We were all dealing with a lot of stuff both professionally and personally, but you know businesses that actually had to be open or make money
00:14:58
Speaker
and that were selling stuff that depended on customers. i mean They were faced with challenges much bigger than anything that I had to deal with. So I actually felt pretty lucky during that time. Now, as GC, of course, mean there's there's still existential threats, at least that we were all very much worried about at the time. um And then and then just the more basic ones, how do you start implementing work from home? from figuring out all the local, you know, because there were the federal regs and the local regs and and and state and then you know you come down to the city in terms of the work from home rules, we did have people who
00:15:35
Speaker
did you know had to be and in what was a hanger at the time we were working out of, to actually physically work on on aircraft. right So we couldn't be fully remote. So there was figuring out sort of the maze of constantly evolving regulation in that regard. There was the, I'd say, uncertainty about the funding environment um that posed challenges. um But in general, I'll say I felt like, again, being in the situation I was in, we we were pretty lucky. So yeah. That's actually a good transition to talk about Arrow. i'm I'm curious, you know, before we talk about the transition to the CEO role and and actually how you got the job at Arrow, when you joined in 2021, right, there were a bunch of COVID restrictions still in place. I'm curious how you helped an airline navigate that, ah because, you know, the business
00:16:30
Speaker
The business clearly survived for a year or two right just from the the sort of halt in air travel. But by the time you joined, there were still a bunch of restrictions on on the operations. um And probably the clientele also had preferences or expectations around what you were going to do to keep them safe, not just in the air, but safe from the air around them. yeah Um, yeah yeah, it was difficult. You know, we had, um, first of all, there were, there were tailwinds, right? Which was is that it's, it's, you know, well-documented that private aviation experienced a surge of growth during, during COVID. Right. And for very obvious reasons, it's you're around less people, yeah which is what, which is what travelers that had the means we' were looking for. Um, so that was a boon to the business and our semi private model.
00:17:23
Speaker
which sort of brings all the benefits of ah private, you know, which you you're going through private terminals, there's less density with the seating, you know, has all those advantages, but with a fraction of the cost that actually finds private or charter that does. um so Again, in that that way, we were we were well situated. Now, of course, the as you mentioned, people were very ah focused on on staying safe. and so A lot of the challenges that we faced weren't worth complying with regulations. that That's the easy thing to do. so When there's a mask mandate, well, you have to wear a mask. There's a mandate.
00:18:00
Speaker
Because when the mandate started to to loosen, actually that the challenges became a little more um complex because you still had groups of travelers who wanted that, who wanted to be around people who were wearing masks. And you had, as you know, we all witnessed you, the the groups of of people who who didn't, and the sort of tension between those two groups would often yeah you know, come to it come to a head. And of course, when that happens on a small airplane, that's not pleasant. We did the best you know, the best that we could to navigate it to keep people safe, but and use common sense. But it was definitely a challenge. The other thing I'll say is we operated at that time in multiple. ah you know We weren't only in the US, but we we're also in Europe at that time.
00:18:47
Speaker
Oh, interesting. It presented its own very complicated challenges because you'd be flying from one place that had a certain set of regulations to another that had a different set of regulations.
Joining Arrow and Dual Role as CEO and Pilot
00:18:57
Speaker
So keeping track of it all was ah was quite challenging. What was it that attracted you to Arrow, sort of taking a step back in the first place? Why did you decide, you know, um this is this is the right next step for me. This is a place that I'm excited about about joining. Well, it was pretty, so how I met, um I'd known Uma Subramanian, the prior CEO.
00:19:20
Speaker
and you know actually i i met her how i met her is a story i want to tell because it just goes to the importance of kind of like getting out there even when you don't feel like it i have to go to to go to industry events and just other ah other things networking whatever it might be so i'd been at the conference for. Vertical take off landing vehicles like the kinds of manufactured by job and archer and others and at the end of it there was a networking event. you know It's like an open bar or something. and I was tired. I'd been there all day. I very much wanted to go home. ah But yeah, I said, you know what? Okay, I'll go. I came out here. I'll go get a drink. and There I met Uma, who was a University of Michigan grad like me, an aviation geek. and We just sort of hit it off and started talking. so We developed a relationship. and In fact, Skyrise, she introduced me to the people at Skyrise, which is how they became a client before I went in-house.
00:20:19
Speaker
And then, yeah, Uma was CEO and she gave me a call one day and said, hey, I'm looking for a GC. Would you be interested? And yeah, I'd love to say that I played hard to get her deliberated. But for me, it was a real, I mean, it was a dream really to go to You know, if i if you think back to where I'd been, and and which was essentially trying to get, you know, wayfinding, you know, doing all these different things to get this opportunity to go in-house to work for a really cool air carrier that flew, you know, sleek black jets to cool places. Yeah. It wasn't hard to say yes to that. Was it part of your negotiation strategy to include the first officer role? ah
00:21:08
Speaker
I don't remember it that way. I've heard it retold that way. but i' know it was it was just you know I came in as a commercial pilot and flight instructor. and so When the time was right, it was something that yeah i thought I thought made sense. um yeah and you know The business gets an additional pilot and I get to learn a lot more about the business at the same time. I'm sure actually that was probably a really important set of learnings about how the business operated, right? Like you really actually got to see it from from the inside, not just from retold, you know, anecdotes from from various folks who who work for the company who are out there in the field. Yeah, I mean, I think that's right. Listen, any time that, you know, ah you're a leader and you get to be involved in sort of the day to day operation of the business, whatever it is you do, you know whether it's it's a restaurant or
00:22:00
Speaker
manufacturing plant it's It's a good thing right to to see, um and in a real hands-on way, you know not just like parachuting onto the factory floor, but to actually participate. um It just teaches you a lot about about what you're doing as a business, about the challenges, um about what your employees are are going through, about what your customers think and need. so yeah i mean it's Being able to fly has been a real... um First of all, it's a privilege and it's a lot of fun. But I also think it's been you know an asset as as ah as a leader and arrow, whether I was GC or now CEO. and It gives me a unique understanding of the business.
00:22:42
Speaker
um Now, that being said, of course, it's not possible for most airline CEOs to also fly the airplanes. Right? Right. You know, Aeros are not a huge company and it'ss it can happen somewhere like that, which is another one of the fantastic things about it. But yeah, like you said it's it's a I very lucky to be able to do it. um But I also think it's um it's ah it's a good thing in my position as CEO that I get to.
00:23:11
Speaker
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00:24:28
Speaker
you know, the, the cockpit to the boardroom in, in any specific circumstances. Yeah. I mean, I i can honestly think of a ah ah ton of them and it's you know from the smallest things like when the network planning team will put out a schedule um and we'll, we'll require, let's say a term to be for, you know, the time between a turn 45 minutes. Right. So when you land to, when you're going to part again, you know, I have a unique, I can, assess whether or not that's a ah feasible amount of time. right Having you know gone through it many times myself, um when it comes to our fueling policy, how much fuel we're going to uplift in certain locations. Fuel in Aspen is much more expensive than it is in, say, Cabo, so we have to be very careful about the way we fuel.
00:25:18
Speaker
i have um experiences that i've I've had fueling have led me to discuss with the team different processes we could have put in place to take advantage of differences in fuel pricing. The list goes on, but there's there's not ah ah a day I fly and probably to the chagrin of many people on the team where I don't come up with some new idea of how to refine or or change what we're doing in the operation based on what I've experienced. I want to ask you a few more sort of questions about the the CEO role. that's That's great. The first is is you know when you made the transition from GC to president to to now CEO, imagine part of that is like you have to build confidence among the investors that you're the the right person. How do you think you you went about that? How did you build that that confidence that that you could take on the CEO role?
00:26:12
Speaker
Well, i mean you'd have to ask them that. ah but but you know listen I think there's a long history of GCs becoming CEOs. right People tend to think, well, it's more of a CFO thing or chief marketing officer thing, but even in the airline industry, um you know some of the the legendary CEOs were actually lawyers, so Herb Keller was know yeah of Southwest fame. Probably the most well-known airline CEO, beloved figure, was ah was the lawyer before he was a CEO. I did not know that. Yep. Interesting. By the way, in practice for a long time, in private practice, um Richard Anderson of Delta,
00:26:57
Speaker
um you know probably the CEO's credited with turning Delta into the the powerhouse that it is today um more than before CEO. I mean, so so the list goes on. so And I think there's a reason ah for that. And that's because you know GCs, I think, you know, as members of the executive team are uniquely sort of touch all different points of the business. um And so get a really deep understanding of how business works as a result of of their role. um Now, of course, you know, CFO and and others do as well. But um I think UC tends to really go deep into many different aspects of the business, because that's what the job requires
00:27:41
Speaker
right Yeah. And then, you know obviously, at the end of the day, being a CEO is about my judgment. There's decision decisions to make, and you bring your judgment to bear when when making those decisions. And you know I think GCs typically are, you know if they're getting to that level, have have their judgment assessed, has been trained, and they're probably pretty strong in that
Leadership and Career Insights at Arrow
00:28:03
Speaker
area. and can then as a litigator even more so. I mean, I think there's there's few crucibles out there for making judgments in ah in a quick and an informed way, and also a relationship with risk, right? Yeah. um I think that GC has also developed a relationship with risk that's a really helpful thing to bring to the to the CEO role. So I'm not sure what of that mix is what ultimately gave the investors confidence, but I think it's those things along with the fact that
00:28:34
Speaker
You know, as GC, depending on the way you've structured it, but youre you have a relationship with the board, right? So they know you're present at board meetings. um They get to see the way you think, um the way you contribute ah to decision making. And I think so, all those things were helpful. With that in mind, I'm very curious about this question and and there'll be some other CEOs on the podcast this season too. Did you feel like you needed to have a mindset shift as you as you took on the CEO role? Did you feel like you needed to sort of maybe affirmatively say, okay, I need to spend a lot more time trying to identify new opportunities for the business or I need to think less about risk or or you know with what you just said in mind,
00:29:18
Speaker
Do you feel like it was it was sort of a natural continuation of the skills that you were already and that the mindset that you were already bringing to bear in your day to day? Yeah, I mean, I'm not sure it was a mindset shift. It was definitely a responsibility shift. right yeah So um there's no doubt about that. you know And to your point of I was spending less time on on certain things, especially legal things than other problems and issues that the business was dealing with. But the mindset is the same, right? I mean, even as GC, um you know I was involved in you know executive level decision making that didn't just concern legal matters. I you know advocated for decisions that I thought were was to make and tried to be as persuasive as I could, even when I was GC. and you know The difference is now, of course, that I am the one making the decision ultimately. But the mindset is, i'd I'd say, at least for me and given in the way that I was operating as GC, ah pretty similar. There's a weight there that there wasn't before. Of course, also, even that you're um you know ultimately responsible for the decision making.
00:30:30
Speaker
But um I think you know if everybody approaches the GC role differently, I'm very much an arrow. And it's because, again, I just have a passion for this, right? it's it was The business itself is why I joined um Arrow to be involved in in in Air Carrier and to to make decisions that went beyond or to be involved in decisions that went beyond just the legal matters. I mean so that's how i approach the gc also is a pretty natural transition how do you feel like ah maybe you've you've worked to manage the rest of your executive team to specific questions in there one behind you needed to do evolve as a manager is the ceo now with a bunch of c-suite direct reports and and make sure they're working really well together.
00:31:15
Speaker
um And then two, I'm really curious about the GC role and and hiring someone for the GC role and advice that you might have for others on that because now you've been on the other side of the table. You're not the one being hired as GC, you're the one doing the hiring. Yeah, so the you know the management piece, I will say that is that that's also just a new skill that and I've had to develop. Yeah. In my entire career, you can actually look over and probably something I shouldn't press up to, but you know I don't have, whether it was in private practice, yeah either at big firms or my own firm where we had a couple associates and a paralegal, when I went in-house, when I was a GC, legal department of one,
00:31:58
Speaker
at both Skyrise and Arrow until I hired about a year before I transitioned into the CD role, I hired a deputy GC at Arrow. So of course, and then to step into a role where where you're you're managing a lot of folks, folks in the C-suite, yeah, there's there's a lot to learn there. The the the benefit or hope that has made it a little bit easier for me is I have a long working relationship with the members of the executive team at Arrow. so I think we've built trust amongst one another because we've operated together ah for so long and they helped me along making this transition. and you know um they're They're fabulous partners. so but That's definitely been something also where I've sought outside counsel on Franklin, just like when I started in the GCU because it's um you something I recognize where I don't have a lot of experience. I look for others for for guidance. and um
00:32:54
Speaker
and help on that. And then um there was a second part to your question. Yeah, it's curious yeah no I was curious. um Now that you're on sort of the other side of the table, hiring someone for a GC position. And and part of that question might also be, you know if you talk to fellow CEOs, advice that you give to them as they look for GCs who they can really sort of truly partner with. Yeah, hiring a GC for a startup type environment is is a hard thing to do. right Because I don't think that there's any specific background that things you need to look for. right You get such varied people who come into these jobs and succeed, whether it's someone who was you know a corporate lawyer at a big firm and then was in-house at a large tech company and then becomes a GC.
00:33:42
Speaker
But to someone like me, with virtually no corporate experience, and it was a litigator and a small firm who comes in and be DGC. And so I think you know the qualities that I always urge people to look for is you know, just someone who's curious and who's excited about the business itself. I mean, I think that that has got to what is what's going to keep this person motivated and and learning and doing frankly, the real tough work that is that of being a GC in a either a legal department, a one or let's say even two or or three. So, you know, I used to say what I hire, when I have hired into that role, it was important for me to find someone who was like,
00:34:24
Speaker
passionate about being at Arrow, ah just because they thought Arrow was a great business, it would be a fun place to work. And I think with that, if you bring that to it and that excitement, you know the the rest of it is going to fall into place. <unk> gonna shoot you know You'll learn what you'll need to learn. You'll find the resources, whether it's internally or externally. But if you don't have that excitement, that spark, it's going to be a really tough slog. And I think that's where I see people fail as GCs when they go places where they just don't have any real passion or excitement for what the company is doing. And that's not to say something's bad about that company. We all get excited about different things. you know I would get much better off getting excited about SaaS or something like that. right i could have
00:35:07
Speaker
you There's places that are going to be they have very lucrative outcomes. But at the end of the day, if you don't have that, um I just don't think you can be your best your best self but at work and really thrive. I love that mentality. A couple more fun questions. I hope they're fun for you that I like to ask most of our guests as we start to wrap up. The first is when I fly, at mostly commercial, unfortunately not on aeroplanes all the time, which would be very comfy. We'll change that. um I hope you do. I hope you fly all over the US s soon. I like to read. I think it's a great time to sort of sit back and and read a book. Anything that you've read recently or, you know, as a part of your career that you'd like to to recommend to to our audience?
00:35:58
Speaker
Yes, but first I want to say that I completely agree with you. And I think one of the great things about flying is the ability to sort of disconnect and yes do things that you don't normally read a novel or whatever it is. But I love doing that too. It's unfortunate that that now, and by the way, ah on Arrow, we have Starlink Wi-Fi. yes ultra fast i mean You can do a Zoom call if you want. It's not good. And you know a lot of the the bigger airlines have increasingly decent Wi-Fi service where you can work. I always kind of keep my fingers crossed and it's getting broken so that I can have an excuse to to read. I agree with you. can You can tell my boss that because I make very clear that I like to read on airlines. Or look out the window. yeah
00:36:48
Speaker
um so in any even i i Unfortunately, I didn't read any of this on an airplane because I've had a very good Wi-Fi recently, but The Wager is a book I recently read. oh yeah ah by Don Gann. It's a fantastic book about basically ah British ships that set sail in the mid 1800s to go intercept a group of Spanish ships off the coast of Patagonia, basically to steal all their their treasure. and They get shipwrecked. It's about the entire voyage.
00:37:24
Speaker
and then just the ah the months that they spend shipwrecked on this desolate post of Chile and um the hardship that they go through, ah the extreme circumstances, and I won't give it away, but it leads to somebody ah some tough stuff. It's it's very it's similar to the um endurance, a great book also about Shackleton, which is one of my favorite books and has this similar thing that's just Shackleton is endurance is a great book about leadership. Shackleton was a phenomenal leader in the fact that he was able to keep his men together and motivated ah for that whole time when and and ultimately led to their to their know ah rescue. This is sort of the opposite of that. This is the story of of of what happens when when leadership
00:38:15
Speaker
um falls apart and and sort of the mutinying and men going out each other in difficult circumstances. But it's it's a great read. Fantastic. ah We must like similar books. I like books that are are nonfiction, but read like fiction. And I'm not totally ashamed of it. I have about 95 tabs open on my iPhone and probably about 60 of them are books I want to read. And both of those are books that are in there. So but your endorsement means that therere they'll be in my ah Amazon or Barnes and Noble cart it's sometime in the next couple of months.
00:38:47
Speaker
ah challenge They're both fantastic. ah My last question for you, Ben, this has been really great that I like to ask all of our guests, which is if you could look back in your days of of being a you know young lawyer, just just starting off at a big firm, something that you feel like you know now that you wish that you'd known back then. and Oh, man, I wish I'd known about discovery. I don't think I would have ever become a litigator if I'd known about discovery. know i um You know, I think what I wish I'd known is I put so much pressure on myself ah to get it right, right out of the gate. um And for some people that happens.
00:39:28
Speaker
and you know, that's great. But I think for a lot of people, when whether it's whether you're a lawyer or not, um there's some wayfinding that's required, right, as you sort of figure out what your place is, and whatever your chosen um of career path is. So I think what I would tell myself now, of course, with with 2020 hindsight is, is not to be so caught up in um thinking you make the perfect decision about your career right out of the gate. But to sort of you know ah approach the process like you would if you were navigating you know and in a car seat and you sort of take a few steps ahead and then every now and then you just reorient yourself. Am I going in the right direction? If not, it's okay to to you know to take a new path.
00:40:15
Speaker
and yeah And hopefully in time, you know, if you keep sort of doing those assessments, um, you'll find yourself where, where you want to and where you should be. So I think that's, that's what I would tell myself now, because I know I was, I was pretty worked up early on about making the right decision every time. This has been a fantastic conversation. Thanks so much for taking the time and joining me for this episode of the abstract. No, it's been fun, Tyler. Thank you. And to all of our listeners, thank you so much for tuning in and we hope to see you next time.